Nitric Acid → Ethyl 2-iodo-4-(trifluoromethyl)-5-thiazolecarboxylate

HRID 1903666Notes

Reaction equation

HRID 1903666 reaction equation
N[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.N([O-])=O.[Na+].[I-:29].[K+]>O>[I:29][C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 4875Potassium IodideHCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 13593392Ethyl 2-iodo-4-(trifluoromethyl)-5-thiazolecarboxylateYield 25.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a cold (-5° C.) solution of 4.0 g (0.0166 mole) of ethyl 2-amino-4-trifluoromethyl-5-thiazolecarboxylate, prepared according to U.S. Pat. No. 2,726,237, in 30 ml. of 85% phosphoric acid and 30 ml. of 70% nitric acid was added a solution of 1.26 g (0.0166 mole) of sodium nitrite in 10 ml. of water in 10 minutes. The reaction mixture was stirred for 10 minutes and poured into a solution of 10 g of potassium iodide in 100 ml. of water. The reaction mixture was stirred overnight and extracted with ether. The ether solution was dried and concentrated and the residue was chromatographed on silica gel to give 1.5 g of the desired product, m.p. 75°-76° C.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-694d565a79954fd9802db40a7a93719f
Source dataset
uspto-grants-1984_03
Patent number
US04437875

Reaction notes

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